Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate

The title mol­ecule, C(20)H(15)NO(3), adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the di­hydro­quinoline unit. In the crystal, corrugated layers are formed by C—H⋯O hydrogen bonds and are stacked by C—H⋯π(ring) inter­actions. Hirshfeld surface analysis indicates that...

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Autores principales: Bouzian, Younos, Chkirate, Karim, Mague, Joel T., Al-Ostoot, Fares Hezam, Hammou Ahabchane, Noureddine, Essassi, El Mokhtar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8340981/
https://www.ncbi.nlm.nih.gov/pubmed/34422309
http://dx.doi.org/10.1107/S2056989021007416
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author Bouzian, Younos
Chkirate, Karim
Mague, Joel T.
Al-Ostoot, Fares Hezam
Hammou Ahabchane, Noureddine
Essassi, El Mokhtar
author_facet Bouzian, Younos
Chkirate, Karim
Mague, Joel T.
Al-Ostoot, Fares Hezam
Hammou Ahabchane, Noureddine
Essassi, El Mokhtar
author_sort Bouzian, Younos
collection PubMed
description The title mol­ecule, C(20)H(15)NO(3), adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the di­hydro­quinoline unit. In the crystal, corrugated layers are formed by C—H⋯O hydrogen bonds and are stacked by C—H⋯π(ring) inter­actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (43.3%), H⋯C/C⋯H (26.6%) and H⋯O/O⋯H (16.3%) inter­actions. The optimized structure calculated using density functional theory at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 4.0319 eV.
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spelling pubmed-83409812021-08-19 Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate Bouzian, Younos Chkirate, Karim Mague, Joel T. Al-Ostoot, Fares Hezam Hammou Ahabchane, Noureddine Essassi, El Mokhtar Acta Crystallogr E Crystallogr Commun Research Communications The title mol­ecule, C(20)H(15)NO(3), adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the di­hydro­quinoline unit. In the crystal, corrugated layers are formed by C—H⋯O hydrogen bonds and are stacked by C—H⋯π(ring) inter­actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (43.3%), H⋯C/C⋯H (26.6%) and H⋯O/O⋯H (16.3%) inter­actions. The optimized structure calculated using density functional theory at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 4.0319 eV. International Union of Crystallography 2021-07-23 /pmc/articles/PMC8340981/ /pubmed/34422309 http://dx.doi.org/10.1107/S2056989021007416 Text en © Bouzian et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Bouzian, Younos
Chkirate, Karim
Mague, Joel T.
Al-Ostoot, Fares Hezam
Hammou Ahabchane, Noureddine
Essassi, El Mokhtar
Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate
title Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate
title_full Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate
title_fullStr Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate
title_full_unstemmed Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate
title_short Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate
title_sort crystal structure, hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di­hydro­quinoline-4-carboxyl­ate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8340981/
https://www.ncbi.nlm.nih.gov/pubmed/34422309
http://dx.doi.org/10.1107/S2056989021007416
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